(1-Benzothiophen-3-yl)boronic acid → (Aminocarbonyl)amino-5-(1-benzothien-3-yl)thiophene-2-carboxamide

HRID 11426

반응식

HRID 11426 반응식
[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8](Br)[S:7][C:6]=1[C:11]([NH2:13])=[O:12])=[O:3].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](B(O)O)=[CH:15]1>COCCOC>[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8]([C:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:14][CH:15]=2)[S:7][C:6]=1[C:11]([NH2:13])=[O:12])=[O:3]

참가 물질

4

반응물 2

HCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 219758555-Bromo-3-ureidothiophene-2-carboxamide

생성물 1

HCID 9836627(Aminocarbonyl)amino-5-(1-benzothien-3-yl)thiophene-2-carboxamide

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

3-[(Aminocarbonyl)amino-5-bromothiophene-2-carboxamide (0.222 g) and 1-benzothien-3-ylboronic acid (0.449 g) were sonicated in 1,2-dimethoxyethane (15 ml) and saturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon. Tetrakis(triphenylphosphine)-palladium (95 mg) was added and the mixture was heated at reflux with stirring for 4.5 h, then allowed to cool and stirred at room temperature overnight. The solution was filtered and washed through with 1,2-dimethoxyethane and water. The filtrate was concentrated in vacuo and taken up in dichloromethane (20 ml) and saturated aqueous sodium hydrogen carbonate solution (20 ml). The solid product was collected by filtration, washed with dichloromethane, water, diethyl ether and dried (226 mg).

후처리

  1. customsaturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon
  2. additionTetrakis(triphenylphosphine)-palladium (95 mg) was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux
  5. temperatureto cool
  6. stirringstirred at room temperature overnight
  7. filtrationThe solution was filtered
  8. washwashed through with 1,2-dimethoxyethane and water
  9. concentrationThe filtrate was concentrated in vacuo
  10. filtrationThe solid product was collected by filtration
  11. washwashed with dichloromethane, water, diethyl ether
  12. customdried (226 mg)

출처 및 근거

ORD 기록
ord-798a65328c5e4ea19223cb360c86736d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098240B2

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